Challenges of Entrepreneurship

–10 Cold, Hard Truths You Need to Know About Before You Can Achieve Success

A lot of entrepreneurs think they need to hustle and push and burn the candle at both ends until they get to the high 6 or 7-figure income mark in their business…and when they get there, they are done!  They made it to Easy Street, so they get to sit back and relax because everything is going to be smooth sailing from here on out.

I have been in business for 17 years now and there is something I have come to understand on a deeper level, something a lot of people don’t see or don’t want to see!  Success isn’t the absence of problems. Success is permission to have bigger problems.

One of my mentors likes to say, “New level, new devil!” and it is 100% true. I wish someone had warned me that challenges and obstacles don’t magically disappear when you get to higher levels of success in your business.

So in today’s post, I am sharing everything I wish someone had told me back in 2003 when I was starting my business.  It is basically a behind-the-scenes look at what really goes down and what you can expect when you hit higher levels of success as an entrepreneur.

Here are the 10 biggest problems faced by successful entrepreneurs that you can look forward to as you scale your business. Yes, I like to call these positive problems, because at the end of the day they are good problems to have!

Positive Problem #1: You Will Be Recognized Whether You Like It Or Not

As your business grows, more people will get to know you and recognize you.  You will receive messages, emails, and texts from people who want to “just chat” or “connect” or “say hey.”  Maybe someone you don’t know stops you on the street and goes…“Hey! I know you! Aren’t you <Sandy Chernoff > from the Soft Skills for Success?”

The only problem with this is a lot of entrepreneurs are introverts and when introverts get a little bit famous, they can start to feel a little awkward because they don’t get to stay anonymous anymore.

The best thing to do here is to decide in advance how much of yourself you want to give to fans and followers in any given situation.  You might find that sometimes your answer is a big fat zero.  This means that if you happen to bump into someone who recognizes who you are, you might have to cut the conversation short and let them know you are late for dinner.  This isn’t about being mean. It is about being smart.  Perhaps over time, you will feel less awkward about these sorts of encounters and so will be able to handle them more easily. I am a very social person so never had trouble with this but can fully understand how a shy person would find this difficult to handle.

When you protect your time and energy, you get to show up fully and serve at the highest level.  You get to give your best to your audience, your clients and your customers… while keeping enough in the tanks for yourself!

Positive Problem #2: You Will Outgrow Some of Your Friends

When I first started my business I had to let go of some of the friends I knew back in my 8 to 4 days of practising dental hygiene.  I found that the more I embraced my new role as an entrepreneur, the less we had in common as they continued along a traditional career and life path.

It quickly got to the point where our conversations became more and more stunted and stilted until we had nothing left to say to each other just to be clear, I still have some friends that I have nothing in common with in terms of what we do for work so it is not just about what you do but who you are.

But here is the thing…  It is super important to know when you have outgrown your social circle as a stilted conversation is usually a great indicator and actively look for new friends who can support who you are becoming and not just who you used to be. People who understand what you are trying to do in your life and your vision for the future, as an entrepreneur.

My advice?  Don’t wait until there is nothing left to salvage. Stay in touch with people you know and like but don’t force friendships to continue if they are not supporting your ongoing evolution.

Positive Problem #3: You Will Get Way Too Many Invites

When you are successful and well-known, lots of people will want you on their podcast /summit/live event and what have you.  Most of these invites will come from people you don’t know.  This isn’t a bad thing and I believe business is about collaboration and connection.  It is never a bad thing to increase your network.

But reputation is everything in business and you don’t want to be in partnership with people who don’t get what it means to build real relationships and lead with value. So don’t hold back…when you receive an invite, ask why they reached out to you and what they are hoping to get from your collaboration.  Ask why they do what they do and ask about their big vision in business and in life.

Go with your gut instinct and learn to tell the difference between people who want to build relationships and share value.  Those who are looking to gain fame or fortune by association.  Essentially people who want to use your reach and your name to forward a hidden agenda usually this has to do with building their list from your audience or selling their programs to your list.

Positive Problem #4: You Will Feel Alone

“It is lonely at the top” isn’t just a popular saying, it is true for many people. As you get to higher and higher levels of success in your business, fewer people will “get” what you are going through, what you are up against and what you want to achieve.  Know that it gets a lot harder to find common ground or camaraderie with people you meet unless you happen to be the kind of person who can create rapport with everyone, which is super rare!

It is why I like to say that the more successful you get, the more you need to get out there and find people who understand what you are going through.  People who want what you want and who will be happy for you when you reach your goals. I have found that one of the best places to connect with like-minded entrepreneurs is inside a business mastermind or at well-run networking groups.  But keep in mind…not all masterminds or networking groups are created equally and you could end up feeling lonelier than ever if you happen to join a group that doesn’t align with your values or your goals.

Positive Problem #5: You May Get Bored 

When you have been teaching the same things and sharing the same message for years, I can pretty much guarantee that boredom will start to set in.  This might seem unbelievable to a lot of enthusiastic, new entrepreneurs who can’t imagine ever being bored with what they do.  But the truth is that boredom is a very real problem as you get more and more successful in your field of expertise because it steals your drive, energy and focus… And it is creative suicide.  I almost never present the exact same workshop as I customize to suit the specific needs of my clients and we explore that in a discussion interview when we first connect.  Not all people who do training take this approach.  It is challenging and time-consuming but I get a lot of very positive feedback from my clients because in the end, they get what they wanted and what they need.

So many successful entrepreneurs are bored out of their minds and they keep going through the motions in their business. The more they are bored, the less creative they get and the less creative they get, the more they are bored and on and on it goes.  Sooner or later, it gets to the point where they quit altogether.   Or they end up running their business into the ground which I often see is a type of self-sabotage and they find a way to end their business just so they can create something fresh and new!

The American illustrator Milton Glaser wrote,

“If you can sustain your interest in what you are doing you are an extremely fortunate person. What you see very frequently in people’s professional lives, and perhaps in their emotional lives as well, is that they lose interest in the third act. You sort of get tired and indifferent, and, sometimes, defensive. And you kind of lose your capacity for astonishment and that is a great loss because the world is a very astonishing place…”

So promise yourself right here, right now that you will do what it takes to keep yourself on the creative edge no matter what.  I want you to pretend you are a “scientist” looking for ways to experiment and shake things up in your business.   For instance, every time I step on stage to teach at an event or present a session that I have taught before, I ask myself, “Where is my edge here?” Am I going to meet their expectations?

Whether it is vulnerability or storytelling or performance or something else… Then I teach at that edge so it is never 100% the same each time.  So whatever you do, never let yourself settle into a “same stuff, different day” mindset.  Avoid getting into a rut or routine that holds you back from experimenting with new business ideas, marketing techniques, or ways of doing business.  Always keep why you are doing what you are doing front and centre.


Sandy Chernoff
Sandy Chernoff
SANDY'S 30 years of didactic and clinical teaching in study clubs and continuing dental education, coupled with her almost 40 years of Dental Hygiene practice bring a wealth of experience to her interactive soft skills workshops. With her education background she easily customizes interactive sessions to suit the specific needs of her clients. Her energetic and humorous presentation style has entertained and informed audiences from Victoria to New York City. Sandy’s client list includes law firms, teaching institutions, volunteer and professional organizations and conferences, businesses, and individuals. Her newest project is turning her live workshops into e-learning programs using an LMS platform. Her teaching and education background have helped her to produce meaningful and somewhat interactive courses for the learners wanting the convenience of e-learning options. As the author of 5 Secrets to Effective Communication, Sandy has demonstrated her ability to demystify the complexities of communication so that the reader can learn better strategies and approaches which will greatly improve their communication skills and ultimately reduce conflict, resentment, disappointment, complaining, and confusion. As a result, the reader will be able to increase productivity, efficiency and creativity, improve all the relationships in their lives and ultimately enjoy a happier, healthier existence! Sandy blogs regularly on her two websites on the various soft skills topics that are featured in her workshops and e-learning programs.

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